The present invention relates to a process for the microbial synthesis of esters from acids.
A process for the preparation of enzyme-mediated synthesis of esters and lactones is set forth in U.S. Pat. No. 4,451,565 issued on May 29, 1984 whereby the enzyme assisted reaction: ##STR4## is disclosed. In the reaction of U.S. Pat. No. 4,451,565, R represents a hydrogen atom or a straight chain or branched saturated or unsaturated hydrocarbon radical which has 1 to 21 carbon atoms and which optionally can be substituted by hydroxyl groups or alkoxy groups with 1 to 10 carbon atoms. R' represents C.sub.1 -C.sub.15 primary or secondary alkyl.
A process for the preparation of terpene alcohol esters by the reaction of terpene alcohols with fatty acids in the presence of selected lipases is described in Japanese Patent Application No. 54/041838. Rodopulo, et al, Chemical Abstracts, Volume 67, 1967, at abstract 10364u (abstract of Vinodel. Vinograd. SSSR 27(3), 15-20 (1967) discloses, in wine fermentation, a process of oxidative deamination accompanied by the generation of alcohols, carbonic acids and ethers "important for the wine bouquet".
Brodelius, et al, European Patent Application No. 18,333 (abstracted at Chem. Abstracts, Volume 94: 63793x) discloses the deamination of methionine having the structure: ##STR5## by means of the fermentation reaction: ##STR6##
Indeed, valine, leucine and isoleucine are shown by Lehninger "Biochemistry", 1975, published by Worth Publishers, Inc. to undergo the following conversions involving:
a. .alpha.-keto-isovaleric acid in the case of valine; PA1 b. .alpha.-keto-.beta.-methyl-valeric acid in the case of isoleucine; and PA1 c. .alpha.-ketoisocaproic acid in the case of leucine, thusly:
__________________________________________________________________________ Sequence "A" Sequence "B" __________________________________________________________________________ ##STR7## ##STR8## ##STR9## ##STR10## ##STR11## ##STR12## ##STR13## ##STR14## ##STR15## ##STR16## ##STR17## ##STR18## ##STR19## ##STR20## ##STR21## ##STR22## ##STR23## ##STR24## ##STR25## ##STR26## ##STR27## ##STR28## ##STR29## ##STR30## ##STR31## ##STR32## ##STR33## ##STR34## ##STR35## ##STR36## ##STR37## ##STR38## __________________________________________________________________________ ##STR39##
In the flavor and fragrance art, a need has arisen for the development and efficient production of naturally occurring carboxylic acid esters which have heretofor been found to be useful and necessary in the creation of flavor formulations used in augmenting or enhancing the aroma or taste of foodstuffs, chewing gums, toothpastes, medicinal products, chewing tobaccos and smoking tobaccos and also useful in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, perfumed polymers, fabric softener compositions, fabric softener articles, hair preparations, cosmetic powders and the like.
U.S. Pat. No. 953,025 issued on Mar. 29, 1910 (Effront) discloses the fermentation reaction of amino carboxylic acids using yeast as the fermentation catalyst to form carboxylic acid thusly: ##STR40##
The "Effront" process is different, in kind, from the process of our invention.
Heretofor, nothing in the prior art discloses either explicitly or implicitly a process for the deamination of naturally occurring amino acid by means of fermentation to yield naturally occurring organoleptically useful esters.